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Organic Chemistry I
CHE 230
Exam 1
February 14
th
Dr. R.W. Nagorski
Science must begin with myths, and with the criticism of myths.
(Karl Popper, 1902-??)
1) ______/6 9) ______/
2) ______/4 10) ______/
3) ______/10 11) ______/
4) ______/8 12) ______/
5) ______/4 13) ______/
6) ______/8 14) ______/
7) ______/4 15) ______/
8) ______/6 16) ______/
17) ______/
Bonus ______/
Total ______/
Name:___________________
ID#:_____________________
CHE 230 – Exam 1 Page 2 February 14 th, 2007
Nomenclature:
Give the IUPAC name for the compounds shown below. (6 points)
Given the IUPAC names below; draw the structure for each compound. (4 points)
a)
b)
c)
a) 3-ethyl-2,2,5,5-tetramethyl-4-(1-methylethyl)heptane
b) 5,9-diethyl-6-methyl-7,8- bis (1,1-dimethylethyl)-4,4-dipropyldodecane
CHE 230 – Exam 1 Page 4 February 14 th, 2007
Name the four intermolecular forces discussed in class and provide a sample compound that would have the named force as its major contributing intermolecular force. (8 points)
Indicate the formal charge on the proper atoms in the structures shown below. No charges are indicated but the molecule could have an overall charge!! (4 points)
Draw the Lewis Structures for the molecules below and using VSEPR Theory, predict the shape of the molecule as dictated by the atom indicated by the arrow ( Be sure to indicate formal charges if they exist ). (8 points)
A) B) O O
H
H H
N
O
H
H
H
A)
B) C 2 H 2
CH 2 O
predict shape of molelcule based upon carbon
predict shape of molelcule based upon carbon
CHE 230 – Exam 1 Initials:_______________________ Page 5 February 14 th, 2007
Circle the major resonance contributor and provide the resonance hybrid for the resonance structures shown below. (4 points)
Give the electronic configuration of nitrogen; draw a second diagram showing how the electronic configuration changes upon the nitrogen becoming sp 2 -hybridized. (6 points)
Name the functional groups indicated by the arrows in the structure shown below. (5 points)
N O
O
O H
O O H HO
HO
O O^ O^ O
CHE 230 – Exam 1 Initials:_______________________ Page 7 February 14 th, 2007
Complete the following Acid/Base reactions or provide products for the reaction. (9 points)
In the molecules below, indicate all bonds that have a dipole and the net dipole moment of the molecule, if one exists? (4 points)
Provide a molecular orbital diagram for H 2 in the space provided below. (4 points)
CH 3
O H
a) b)^
Br
Br
H
H
a) (^) +
b) (^) +
c) +
CH 3
H H
AlCl (^3)
H H
O
OH
O
O
CHE 230 - Exam 1 Page 8 February 14 th, 2007
- For the potential energy diagram below, draw the correct Newman projection for each of the staggered and eclipsed conformations for rotation about the C2-C3 bond (indicated by the arrow) of 2-methylbutane at the correct positions of the potential energy diagram. (7 points)
E
N
E
RGY
Group***Period
(^1) IA1A
(^2) IIA2A
(^3) IIIB3B
(^4) IVB4B
(^5) VB5B
(^6) VIB6B
7 VIIB7B
8 VIII
8
(^9) VIII 8
(^10) VIII^8
11 IB1B
(^12) IIB2B
(^13) IIIA3A
(^14) IVA4A
(^15) VA5A
(^16) VIA6A
(^17) VIIA7A
18 VIIIA
8A
1
(^1) H1.
(^2) He
2
(^3) Li6.
(^4) Be9.
(^5) B
(^6) C
(^7) N14.
(^8) O
(^9) F19.
(^10) Ne20.
3
(^11) Na22.
(^12) Mg24.
(^13) Al26.
(^14) Si28.
15 P30.
16 S32.
(^17) Cl35.
(^18) Ar39.
4
(^19) K39.
(^20) Ca40.
(^21) Sc44.
(^22) Ti47.
(^23) V50.
(^24) Cr52.
(^25) Mn54.
(^26) Fe55.
(^27) Co58.
(^28) Ni58.
(^29) Cu63.
(^30) Zn65.
(^31) Ga69.
(^32) Ge72.
(^33) As74.
(^34) Se78.
(^35) Br79.
(^36) Kr83.
5
(^37) Rb85.
(^38) Sr
(^39) Y
(^40) Zr91.
(^41) Nb92.
(^42) Mo95.
(^43) Tc(98)
(^44) Ru101.
(^45) Rh102.
(^46) Pd106.
(^47) Ag107.
(^48) Cd112.
(^49) In114.
(^50) Sn118.
(^51) Sb121.
(^52) Te127.
53 I 126.
(^54) Xe131.
6
(^55) Cs132.
(^56) Ba137.
57 La*138.
(^72) Hf178.
(^73) Ta180.
(^74) W183.
(^75) Re186.
(^76) Os190.
(^77) Ir190.
(^78) Pt195.
(^79) Au197.
(^80) Hg200.
(^81) Tl204.
(^82) Pb207.
(^83) Bi209.
(^84) Po(210)
(^85) At(210)
(^86) Rn(222)
7
(^87) Fr(223)
(^88) Ra(226)
89 Ac**
(227)
(^104) Rf(257)
(^105) Db(260)
(^106) Sg(263)
(^107) Bh(262)
(^108) Hs(265)
(^109) Mt(266)
(^110) Uun()
(^111) Uuu()
(^112) Uub()
(^113) Uut()
(^114) Uuq()
(^115) Uup()
(^116) Uuh()
(^117) Uus()
(^118) Uuo()
